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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 539657Generated: October 25, 2026

Water → Methyl 5-methyl-2-(pyridin-4-yl)benzoate

https://huagongshe.com/reaction/539657

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium CarbonateHCID 10340—
Reactant(Pyridin-4-yl)boronic acidHCID 2734379—
ReactantMethyl 2-bromo-5-methylbenzoateHCID 15110996—
CatalystHCID 178418397HCID 178418397—
Solvent1,2-DimethoxyethaneHCID 8071—
SolventEthyl AcetateHCID 8857—
ProductMethyl 5-methyl-2-(pyridin-4-yl)benzoateHCID 8668084148.5%

Reaction Steps

A mixture of methyl 2-bromo-5-methylbenzoate (5.2 g), pyridine-4-boronic acid (4.2 g), sodium carbonate (4.8 g), tetrakis(triphenylphosphine)palladium(0) (1.3 g), water (10 mL) and DME (50 mL) was heated under reflux overnight under a nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate, and filtered through silica gel. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.5 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08871766B2
Source datasetuspto-grants-2014_10
ORD IDord-70d53f886ec9452084e592c74feaa7d6
Source noteuspto-grants-2014_10